Rough and Rowdy Ways Part 4: The Rubicon to Key West

by Stephen Scobie

Previously in this series

“Crossing the Rubicon”

I crossed the Rubicon on the 14th day
Of the most dangerous month of the year

What would Julius Caesar do?  Well, one answer is that he would lead his army across the River Rubicon, thus precipitating Civil War in Rome.  So this action has become emblematic of a decisive and irrevocable act, a calculated risk, a breaking of taboos.  In Caesar’s case, it worked – but  there are no guarantees for prospective crossers.

Why the 14th day of an unnamed month?  The best known historical reference for that date would be July 14th: the storming of the Bastille, the beginning of the French Revolution, an ideal example of Rubicon crossing.  And July is, of course, the month named in honour of Julius Caesar – who actually crossed the river in January.  But there is also September 14th, 1901, date of the assassination of William McKinley: see below, the opening lines of “Key West.”

I painted my wagon, abandoned all hope.

“Paint your wagon” is a colloquial phrase for getting things ready to be done, deciding to act – not quite as drastic as crossing the Rubicon, but getting there.  Also the title of a 1969 movie musical starring, incongruously, Clint Eastwood.   And remember the “painted wagon” in “Senor” (1978).

“Abandoned all hope” comes from Dante’s Inferno: it is the inscription above the Gate of Hell.  Translations vary between “Abandon all hope, ye who enter here” and “Abandon hope, all ye who enter here.”        

Well, the Rubicon is a red river

But it’s not the only one.  There is a Red River in Dylan’s home state of Minnesota.  There is a great 1948 western movie called Red River, whose plot has several echoes in RRW.  In 1997, Dylan recorded a wonderful song called “Girl from the Red River shore.”

I can feel the bones beneath my skin

It’s a bit of a stretch, but I cannot resist the echo from T.S. Eliot, “Whispers of Immortality,”  “Webster was much possessed with death / And saw the skull beneath the skin.”

And here again are the threats of violence –

I’ll make your wife a widow
You’ll never see old age….
I’ll cut you up with a crooked knife

And yet here too, in the midst of these threats, we come to the most explicitly redemptive lines on the whole album:

I feel the Holy Spirit inside
See the light that freedom gives
I believe it’s in the reach of
Every man who lives

— punctuated by an almost off-microphone “O Lord!”

Mona, baby, are you still in my mind?

Are we all the way back to 1966, “Memphis Blues Again,”  “Mona tried to tell me / To stay away from the train line”?  Or is it Lisa again?

“Key West (Philosopher Pirate)”

 Key West is, Dylan’s song tells us, “on the horizon line.”   It’s as far as you can go in one direction of America: the limit, the end.  But like a horizon, it recedes: it is always just beyond reach.  It is posited as an ideal, never quite attainable, but possibly imaginable in one particular place: Key West.

Historically, Key West has long been seen as a refuge, for pirates (such as one 18th century predator named Black Caesar!), or for writers, from Ernest Hemingway to Wallace Stevens.  (There is no doubt a whole article to be written on the links between Dylan’s song and Stevens’ poem “The Idea of Order at Key West,” but I’m sorry, I don’t feel up to attempting that one.)  The New Basement Tapes, the 2014 collection of songs based on texts written by Dylan in 1967 but left unfinished, contains one track entitled “Florida Key,” which also evokes the idea of an ideal destination.

But before we even get started, and despite the dreamy music in the background, there is a violent interruption:

McKinley hollered, McKinley squalled,
Doctor said McKinley, death is on the wall

The first two lines of Dylan’s song are the same as the first two lines of “White House Blues,” a 1926 song by Bill Monroe, lamenting the death of William McKinley, 25th President of the United States, who was assassinated in Buffalo, NY, on September 14th, 1901.  (See “Crossing the Rubicon” for another 14th.)  I am not aware of any special connection between McKinley and Key West   He appears here mainly as a signpost towards that huge song looming just ahead, “Murder Most Foul,” where his memory will hang in the background list of the four assassinated Presidents: Lincoln, Garfield. McKinley, Kennedy.  Still, it is an odd way to begin a song about an idyllic ideal.  As if, before the “idea of order” has even been established, it has to be brought violently back down to earth,  Later in the song, there will be another violent interruption.

Down in the boondocks

 See “Murder Most Foul.”

I’m looking for love, for inspiration
On that pirate radio station
Coming out of Luxembourg and Budapest

Key West always welcomed pirates, such as Black Caesar.  The term “pirate radio station” dates from Britain in the 1950s, when Radio Luxembourg operated outside the tight constraints of BBC regulation.  Many a British teenager lay awake at night listening to Radio Luxembourg beneath the pillows.  Later, the most famous pirate station was Radio Caroline, operating from a ship in the North Sea, forever patrolling just outside British territorial waters.  I am not familiar with the history of pirate radio in Hungary,  Maybe it’s just that Budapest rhymes with Key West.

Down in the flatlands

Not quite “Lowlands,” but almost.

Key West is the place to be
If you’re looking for immortality…
If you lost your mind, you’ll find it there

At the expense of a somewhat clumsy rhyme, this is the song’s most direct statement of the ideal waiting on, or beyond, the horizon line.

Like Ginsberg, Corso and Kerouac

Allen, Gregory, Jack.  A triumvirate of the Beat Generation.  In 1954, Ginsberg recorded a song playing variations on “When the Saints Go Marchin’ in.”  It’s called “Walking at Night in Key West.”

Like Louis and Jimmy and Buddy and all the rest

Take your pick.  I guess Armstrong, Reed, and Holly, but the possibilities are endless.

Got my right hand high, with the thumb down

Again, justice as violence.  Thumb down is now generally accepted as a sentence of death.  (There is a memorable thumbs down in Spartacus.)  It was not ever thus.  In Roman times, and right up until just a couple of hundred years ago, it was the other way round.  Thumbs down asked the victorious gladiator to plunge his sword or spear into the ground, sparing the defeated opponent.  Thumbs up signalled that the death blow should come higher, into the heart or neck.

Down on the bottom

 The New Basement Tapes also contains a song called “Down on the Bottom.”  Perhaps Dylan did scavenge some lines from his earlier, forgotten, and newly rediscovered self.

I’ve never … wasted time with an unworthy cause

Recall “Restless Farewell”  (1964): “The cause was there before I came.”

Newton Street, Bayview Park….

Most of the street names in this song do show up on Internet searches of Key West street names.  Bayview Park is actually on Truman Avenue.  The only one I haven’t found is, perhaps unsurprisingly, History Street.  President Truman did have a Southern White House in Key West.  But he is one of the few Presidents named on this album who was not  assassinated.

Twelve years old, they put me in a suit
Forced me to marry a prostitute

What??  This is clearly a fiction, which (like “I shot a named Grey” in “Tangled Up In Blue”) is so obviously outrageous that it can only be seen as disrupting and blocking any autobiographical reading.  Like the first (McKinley) verse, it comes as a violent disruption of the ideal – which it then attempts to redeem: “we’re still friends”.


So we come to the place where, if you’re going to listen to RRW all the way through, you have to get up from your chair, take out the first CD, fetch the second, put it on, settle back for another 17 minutes.  Many people, I suspect, may let it pass, treating RRW as a 9-song CD, ending with “Key West” – which gives that song a special emphasis, as the “last” song on the album, a position usually reserved by Dylan for definitive statements, from “Restless Farewell” to “Desolation Row” to “Dark Eyes” to “Ain’t Talking.”  And, of course, “Sad Eyed Lady of the Lowlands,” the only other song to occupy the whole of a single LP side, or a single CD.  “Murder Most Foul” is thus both an end and a new beginning.

It was the first song from the album to be released, and it was a bombshell.  There had been no advance publicity, not even rumours of its existence.  I remember getting up one morning, checking my computer, and starting to play a song logging in (surely a mistake!)  at 17 minutes,  (Actually a few seconds shorter, but 17 sounded conclusive.)   I understand that, technically, it could have fit on a single CD.  Setting it apart on a separate disc was a deliberate choice, giving it even greater prominence – which I, as listener, reinforce every time I get up to change the disc.

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  1. Wallace’s “Key West” can be interpreted as an artist imposing his/her own order on Nature and Society rather than merely reflecting it – ie,Virgil’s ‘Aeneid’.

    Analogically, parental pre-arranging marrages of offspring impose a strict order on social relations .

  2. ‘the 14th day
    Of the most dangerous month of the year’
    Probably, already been remarked upon, but the 14th was also the day before the ides of March, the day on which Caesar was assassinated. In the Roman calender, the ides could also refer to the 15th of May, July or October.
    Julius Caesar, the first( among equals) in Dylan’s list of assassinated heads of state.

  3. “Red River Shore” is the correct title of Dylan’s song…be wary of us “ant-f*ckers” lurking around, who are ready to pounce on unsuspecting prey!

  4. Rather than to the John Wayne cattle-driving movie, Dylan’s song seems to relate more to the original version of the song “The River Valley”(in Manitoba) in which a soldier from eastern Canada deserts a French/Indian maiden who loves him, to whom she must sadly say ‘adieu’ (in Dylan’s rendition, the woman advises her lover to ‘go home’.

    The original Canadian song later gets transferred to the Red River in the US south, and references a ‘cowboy’ instead.

  5. This is not to say that Dylan isn’t alluding to the western song in which it is
    the woman who leaves the southern Red River Valley – leaving behind her
    French- speaking cowboy – sung by Mary Robbins, for example.

  6. Everyone knows it was Oscar Wilde’s sharp pen that killed Dorion Gray(sic), and tried to frame Dylan for doing the dastardly deed….Gray’s proposeded marriage never happened so Bob could not have run off with his wife to Italy….not to mention that she had already killed herself.

  7. i believe the 14th day of the most dangerous month is APRIL….titanic sunk, lincoln killed, big dust storm….see gillian welch & david rawlings songs (there are 2)

  8. Regarding being married to a prostitute:
    Hosea 1:2 “The Lord said to Hosea, ‘Go, take to yourself a wife of whoredom and have children of whoredom.’”
    Maybe, the exegesis on this is relevant as it applies to a promised land, or perhaps a shimmering vision, such as Key West.

  9. Indeed, Hosea’s would be a pre-ordained wedding for sure – the Lord regarding nearly all Northern Israelites as prostitutes and idol worshippers – fits in with the idea of Key West (akin to split- in-half Israel)being like the corrupted
    two -pathed Underworld that Virgil describes in the ‘Aeneid.’

  10. It hit me that the 12 year old in a suit marrying a prostitute was his bar mitzvah. Key West is “paradise” and about as far from Hibbing as you can go. The whole album is a reflection on a life (career, touring) winding down. He has to adjust and that includes assessing his spiritual side. Maybe I’m way off, but who really knows. Great album.

  11. “Red River Shore” is a move starring Rex Allen who sings ‘Red River Valley’.

  12. Gene Autry stars in movie called ‘Red River Valley’, sings the song.

    Roy Rogers stars in a movie called ‘Red River Valley’, sings the song.

  13. In the Key West song Dylan mentions Truman. Harry Truman ordered the bombing of Hiroshima and Nagasaki. On the 6th of August 1945 the Little Boy was detonated in Nagasaki and 3 days later on the 9th of August 1945 another bomb called Fat Man hit Nagasaki. Apparently Truman didn’t loose his sleep over this decision (according to his own statement).

  14. Re: “Luxemburg & Budapest”

    Radio Luxemburg was, I would contend, never classed as a pirate station given its status within a sovereign country. Unlike Caroline, London etc.

    But this fine detail would most likely have been lost on Dylan in his first trips to London from 1963 onwards.

    Budapest might well be an allusion to the Soviet invasion of Hungary in October 1956. It was before television became pervasive in Europe and, very significantly, the “rebels” who were crushed by the Russian tanks, used Radio Budapest to appeal, forlornly for outside help.

    This poignant message will have struck very deep with 15 year old Bobby Zimmerman, I feel sure.

  15. I spotted a mistake I made which I want to correct. A bomb called “Little Boy” was dropped on Hiroshima (not on Nagasaki). By the way I can’t believe that somebody could call a weapon of mass destraction “Little Boy”!!!. It is evil in itself. The bomb which killed innocent civilians given such an innocent, even sweet name!?!? What can be more innocent than a child? A little boy or a girl for that matter. Little boy come blow your horn!!!

  16. Crossing the Rubicon:

    Verse 1: She is speaking. She took the wrong path: ‘I abandoned all hope’
    Verse 2: Devil is speaking. ‘Three miles north of purgatory – one step from the great beyond, I prayed to the cross and I kissed the girls’
    Verse 3: He is speaking. ‘How much longer can it last – how long can this go on, I embraced my love put down my head’, he has lost her love.
    Verse 4: Devil is speaking. ‘I’ll make your wife a widow – you’ll never see old age’
    Verse 5: He is speaking. ‘Put my heart upon the hill where some happiness I’ll find’ He’s takes the right path.
    Verse 6: Devil is speaking. ‘I’ll cut you up with a crooked knife and I’ll miss you when you’re gone’ (sarcastic mode)
    Verse 7: She is speaking, talking to her self. ‘You won’t find any happiness here – no happiness or joy, Go back to the gutter (note another Dylan lyric ‘ picked you up from the gutter and this is the thanks I get’) and try your luck – find you some nice young pretty boy, Tell me how many men I need and who I can count upon.’ She is searching for love and can’t find it because she took the wrong path.
    Verse 8: He is speaking: ‘I feel the Holy Spirit inside and see the light that freedom gives.’ (He is Dylan if you had not noticed it yet.)
    Verse 9: Devil is speaking. ‘The killing frost is on the ground and the autumn leaves are gone, I lit the torch and I looked to the east.’ The devil thinks that she is still in his power.

  17. ‘I’m looking for love, for inspiration
    On that pirate radio station
    Coming out of Luxembourg and Budapest’

    ‘Luxembourg’ Elvis Costello, ‘Budapest’ George Ezra.

    ‘Twelve years old, they put me in a suit
    Forced me to marry a prostitute’

    ’12 Years Old’ Kim Stockwood:

    Cuz I feel like I’m 12 years old
    And I feel like I’m in the cold
    And I feel like I’m 12 years old
    How could it be that you’re so vain?
    And how can it be that I’m such a pain?
    Why can’t you see this time you’ve gone too far?
    Today I couldn’t care less where you are
    Cuz I feel like I’m 12 years old
    And I feel like I’m in the cold
    And Im all alone

    He married Sarah, not really a prostitute. Maybe from the idea that you are still in love with another woman?

    Enough reasons to look for more songs in Key West, I found 50 old and new songtitles, all the artists writing about heartbreak. The title has a number in the song, see below for the artist.

    McKinley hollered – McKinley squalled
    Doctor said McKinley – death is on the wall(1)
    Say it to me if you got something to confess
    I heard all about it – he was going down slow(2)
    Heard it on the wireless radio
    From down in the boondocks(3) – way down in Key West

    I’m searchin’ for love and inspiration
    On that pirate radio station
    It’s comin’ out of Luxembourg(4) and Budapest(5)
    Radio signal(6) clear as can be(7)
    I’m so deep in love(8) I can hardly see(9)
    Down in the flatlands(10) – way down in Key West

    Key West is the place to be
    If you’re lookin’ for immortality(11)
    Stay on the road(12) – follow the highway sign
    Key West is fine and fair
    If you lost your mind(13), you’ll find it there
    Key West is on the horizon line(14)

    I was born on the wrong side of the railroad track(15)
    Like Ginsberg, Corso and Kerouac
    Like Louie and Jimmy and Buddy and all of the rest
    It might not be the thing to do
    But I’m stickin’ with you(16) through and through(17)
    Down in the flatlands – way down in Key West

    I got both my feet planted square on the ground
    Got my right hand high with the thumb down
    Such is life(18) – such is happiness(19)
    Hibiscus flowers grow everywhere here
    If you wear one put it behind your ear
    Down on the bottom – way down in Key West

    Key West is the place to go
    Down by the Gulf of Mexico(20)
    Beyond the sea(21) – beyond the shifting sand(22)
    Key West is the gateway key
    To innocence and purity
    Key West – Key West is the enchanted(23) land

    I’ve never lived in the land of Oz
    Or wasted my time with an unworthy cause
    It’s hot down here and you can’t be overdressed
    The tiny blossoms of a toxic plant
    They can make you dizzy – I’d like to help ya but I can’t
    Down in the flatlands – way down in Key West

    The fishtail ponds and the orchid trees
    They can give you the bleedin’ heart disease
    People tell me – I oughta try a little tenderness(24)
    Amelia(25) Street – Bay View(26) Park
    Walkin’ in the shadows after dark(27)
    Down under – way down in Key West

    I play the gumbo limbo(28) spirituals
    I know all the Hindu rituals
    People tell me that I’m truly blessed(29)
    Bougainvillea(30) bloomin’ in the summer and spring
    Winter here is an unknown thing
    Down the flatlands – way down in Key West

    Key West is under the sun(31)
    Under the radar – under the gun(32)
    You stay to the left and then you lean to the right
    Feel the sunlight on your skin(33)
    And the healing virtues of the wind
    Key West – Key West is the land of light

    Wherever I travel – wherever I roam(34)
    I’m not that far from the convent(35) home
    I do what I think is right – what I think is best
    Mystery Street(36) off Mallory(37) Square
    Truman had his White House there
    Eastbound – westbound
    Way down in Key West

    Twelve years old(38) and they put me in a suit
    Forced me to marry a prostitute
    There were gold fringes on her wedding dress(39)
    That’s my story(40) but not where it ends(41)
    She’s still cute and we’re still friends(42)
    Down in the bottom – way down in Key West

    I play both sides against the middle(43)
    Pickin’ up that pirate radio signal(44)
    I heard the news(45) – I heard your last request(46)
    Fly around my Pretty Little Miss(47)
    I don’t love nobody(48) – gimme a kiss(49)
    Down at the bottom(50) – way down in Key West

    Key West is the place to be
    If you’re lookin’ for immortality
    Key West is paradise divine
    Key West is fine and fair
    If you lost your mind you’ll find it there
    Key West is on the horizon line

    1. Richard & Linda Thompson, ‘Wall Of Death’
    2. Howlin’ Wolf, ‘Goin Down Slow’
    3. Joe South, ‘Down In The Boondocks’
    4. Elvis Costello, ‘Luxembourg’
    5. George Ezra, ‘Budapest’
    6. The Mammals, ‘Radio Signal’
    7. Scotty McCreery, ‘Clear As Day’
    8. Deniece Williams, ‘So Deep In Love’
    9. Conway Twitty, ‘I Can’t See Me Without You’
    10. Don Williams, ‘Flatlands’ (album)
    11. Céline Dion, ‘Immortality’
    12. Corinne May, ‘Stay On The Road’
    13. Billie Eilish, ‘Lost My Mind’
    14. Mike Gordon, ‘Horizon Line’
    15. Dr John, ‘On The Wrong Side Of The Railroad Tracks’
    16. Jimmy Bowen, ‘I’m Stickin’ With You’
    17. Khai Dreams, ‘Through And Through’
    18. Rank 1, ‘Such Is Life’
    19. Gavin Rossdale, ‘This Is Happiness’
    20. Clint Black, ‘Gulf Of Mexico’
    21. Bobby Darin, ‘Beyond The Sea’
    22. The West Coast Pop Art Experimental Band, ‘Shifting Sand’
    23. Taylor Swift, ‘Enchanted’
    24. Otis Redding, ‘Try A Little Tenderness’
    25. Joni Mitchell, ‘Amelia’
    26. Lenzman, ‘Bayview’
    27. Ana Popovic, ‘Shadow After Dark’
    28. New Normal Funk, ‘Gumbo Limbo’
    29. Teddy Pendergrass, ‘I’m Truly Blessed’
    30. Dickey Betts, ‘Bougainvillea’
    31. DIIV, ‘Under The Sun’
    32. Randy Newman, ‘Under The Gun’
    33. Lil Peep, ‘Sunlight On Your Skin’
    34. Woody Guthrie (from ‘Ramblin’ Reckless Hobo’)
    35. Corbin, ‘Convent’
    36. Alma Cogan, ‘Mystery Street’
    37. David Gray, ‘Mallory’
    38. Kim Stockwood, ’12 Years Old’
    39. Taeyang, ‘Wedding Dress’
    40. Collin Raye, ‘That’s My Story’
    41. Corrie Underwood, from ‘See You Again’
    42. Donnie Hathaway, ‘We’re still friends’
    43. Jackie Moore, ‘Both Ends Against The Middle’
    44. The Mammals, ‘Radio Signal’
    45. David Johansen, ‘Heard The News’
    46. Paolo Nutini, ‘Last Request’
    47. Patty Loveless, ‘Pretty Little Miss’
    48. Spinners, ‘Love Don’t Love Nobody’
    49. Van Morrison, ‘Gimme A Kiss’
    50. Dragibus, ‘Down At The Bottom’

  18. Edit: Mammals with ‘Radio Signal’ are mentioned twice, therefore number 44 has to be removed.
    Extra: Built to spill, ‘Fly Around Pretty Little Miss’ between 46 and 47.
    Makes 50 again.

  19. I think it should be 60 songs just like the book that comes out.
    I know I have missed a few:
    Chris Brown, ‘Say It To Me’
    Twinkids, ‘Overdressed’
    NOFX – ‘Bleedin Heart Disease’
    Tommy Roe, ‘Dizzzy’
    Wolfgun, ‘Summer & Spring’
    Underworld, ‘Underneath the radar’
    ‘Tonetta, ‘Marry a prostitute’ (does this artist sings about heartbreak? Yes, see for instance ‘I’ll Remain As I Am’)
    Little Feat, ‘Way Down Under’

    Lyric change in live concerts 2022:
    ‘Down In The Boondocks’ into ‘Early One Morning’, traditional.
    ‘Flatlands’ into ‘Way Down Here’, that’s a song by Kenny Chesney.

  20. And:
    Salena Jones – Love & Inspiration
    Freedom Call – Land Of Light

    Makes 60.

  21. Lookie here- a very flawed interpretation above…

    He who’s sure he has the story line of “Rubicon” all figured out (ie, as to who’speaking) commits the sin of hubris ..,..better to say this is how “I” interpret the lyrics.

    Otherwise it’s rotten tomatoes all round.

  22. Anyway, for what it’s worth, in the “Inferno”, it’s female Beatrice, akin to Mona, who eventually guides Dante in the Underworld so he can have a look at Paradise after going through Purgatory and Hell.

  23. But first she has to escape from her now husband Lucifer’s hold on her; apparently Dante had done her wrong for which she hadn’t forgiven him.

  24. In the concert of October 5, Berlin, I hear Dylan emphasize ‘Pirate Radio Signal’! Oh dear, missed a very important one:

    Randy Newman – ‘Pirate Radio’ (2001) but Newman has already been mentioned with ‘Under the gun’. That certainly has to be:

    The Black Keys – ‘Under The Gun’ (2019)

    Others I’ve found:

    Andy Bey – ‘Hibiscus’ (1974)
    Default – ‘Wasting My Time’ (2001)
    Alanis Morisette – ‘Orchid’ (2008)
    Flaming Ember – ‘Westbound #9’ (1970)

    All 100% sure, given the other lyrics on the CD’s they are on.

  25. Two more:
    Joe Cocker – ‘Highway highway’
    Rich Mullins – ‘Both feet on the ground’

    = 67, I would like to remove number 41 because it is not from a song title.

    Makes 66.

  26. In the Philosopher modern songbook we have My Fair Lady, here we have The Wizard of Oz, that’s why I want to add ‘Land of Oz’. To keep 66 songs I’m removing the album song title ‘Flatlands’, Don Williams.
    NB Also, all the songwriters in the Philosopher Modern Song Book are writers about the same kind of heartbreak and many of them also appear in Theme Time Radio Hour.

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